Sodium Chloride → HCID 12967236, compound

HRID 324176Notes

Reaction equation

HRID 324176 reaction equation
[C:1]([C:5]1([OH:20])[C:9]([CH3:11])([CH3:10])[CH2:8][O:7][CH:6]1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.C1C(=O)N([Br:33])C(=O)C1.[Cl-].[Na+]>O>[Br:33][C:15]1[CH:16]=[CH:17][C:12]([CH:6]2[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([OH:20])[C:9]([CH3:11])([CH3:10])[CH2:8][O:7]2)=[CH:13][C:14]=1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 67184N-bromobutanimide2×HCID 12967235HCID 12967235, compound2×

Product 1

HCID 12967236HCID 12967236, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Adding 2.16 g (7.77 mmol) of 3-t-butyl-3-hydroxy-2-(3-methoxyphenyl)-4,4-dimethyl-2,3,4,5-tetrahydrofuran (Compound [50]) to the mixture of 20 ml of THF and 2 ml of H2O, the mixture was stirred at the temperature of 0° C. After adding 1.54 g (8.65 mmol) of NBS, the mixture was stirred over night with increasing the temperature to a room temperature gradually, 140 mg (0.787 mmol) of NBS was added and the mixture was stirred for 6 hours. The mixture was added to saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic layer was washed with a solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride in this order, then dried with magnesium sulfate anhydride and concentrated. The concentrate was crystallized with the mixture of hexane and ethyl acetate to obtain 1.323 g of 2-(4-bromo-3-methoxyphenyl)-3-t-butyl-3-hydroxy-4,4-dimethyl-2,3,4,5-tetrahydrofuran (Compound [51]). Yield 47.7%

Workup

  1. stirringthe mixture was stirred over night
  2. temperaturewith increasing the temperature to a room temperature gradually
  3. stirringthe mixture was stirred for 6 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a solution of sodium thiosulfate
  6. dry with materiala saturated aqueous solution of sodium chloride in this order, then dried with magnesium sulfate anhydride
  7. concentrationconcentrated
  8. customThe concentrate was crystallized with the mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-54b04b4ba32a4884a332e71f6431f27d
Source dataset
uspto-grants-2001_04
Patent number
US06218135B1

Reaction notes

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